Recent developments in enantioselective photocatalysis

Callum Prentice,
James Morrisson,
Andrew D. Smith and
Eli Zysman-Colman

Review
Published 29 Sep 2020

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1. Graphical Abstract
2. Scheme 1: Amine/photoredox-catalysed α-alkylation of aldehydes with alkyl bromides bearing electron-withdrawi...
  
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3. Scheme 2: Amine/HAT/photoredox-catalysed α-functionalisation of aldehydes using alkenes.
  
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4. Scheme 3: Amine/cobalt/photoredox-catalysed α-functionalisation of ketones and THIQs.
  
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5. Scheme 4: Amine/photoredox-catalysed α-functionalisation of aldehydes or ketones with imines. (a) Using keton...
  
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6. Scheme 5: Bifunctional amine/photoredox-catalysed enantioselective α-functionalisation of aldehydes.
  
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7. Scheme 6: Bifunctional amine/photoredox-catalysed α-functionalisation of aldehydes using amine catalysts via ...
  
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8. Scheme 7: Amine/photoredox-catalysed RCA of iminium ion intermediates. (a) Synthesis of quaternary stereocent...
  
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9. Scheme 8: Bifunctional amine/photoredox-catalysed RCA of enones in a radical chain reaction initiated by an i...
  
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10. Scheme 9: Bifunctional amine/photoredox-catalysed RCA reactions of iminium ions with different radical precur...
  
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11. Scheme 10: Bifunctional amine/photoredox-catalysed radical cascade reactions between enones and alkenes with a...
  
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12. Scheme 11: Amine/photocatalysed photocycloadditions of iminium ion intermediates. (a) External photocatalyst u...
  
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13. Scheme 12: Amine/photoredox-catalysed addition of acrolein (94) to iminium ions.
  
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14. Scheme 13: Dual NHC/photoredox-catalysed acylation of THIQs.
  
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15. Scheme 14: NHC/photocatalysed spirocyclisation via photoisomerisation of an extended Breslow intermediate.
  
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16. Scheme 15: CPA/photoredox-catalysed aza-pinacol cyclisation.
  
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17. Scheme 16: CPA/photoredox-catalysed Minisci-type reaction between azaarenes and α-amino radicals.
  
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18. Scheme 17: CPA/photoredox-catalysed radical additions to azaarenes. (a) α-Amino radical or ketyl radical addit...
  
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19. Scheme 18: CPA/photoredox-catalysed reduction of azaarene-derived substrates. (a) Reduction of ketones. (b) Ex...
  
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20. Scheme 19: CPA/photoredox-catalysed radical coupling reactions of α-amino radicals with α-carbonyl radicals. (...
  
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21. Scheme 20: CPA/photoredox-catalysed Povarov reaction.
  
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22. Scheme 21: CPA/photoredox-catalysed reactions with imines. (a) Decarboxylative imine generation followed by Po...
  
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23. Scheme 22: Bifunctional CPA/photocatalysed [2 + 2] photocycloadditions.
  
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24. Scheme 23: PTC/photocatalysed oxygenation of 1-indanone-derived β-keto esters.
  
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25. Scheme 24: PTC/photoredox-catalysed perfluoroalkylation of 1-indanone-derived β-keto esters via a radical chai...
  
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26. Scheme 25: Bifunctional hydrogen bonding/photocatalysed intramolecular [2 + 2] photocycloadditions of quinolon...
  
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27. Scheme 26: Bifunctional hydrogen bonding/photocatalysed intramolecular RCA cyclisation of a quinolone.
  
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28. Scheme 27: Bifunctional hydrogen bonding/photocatalysed intramolecular [2 + 2] photocycloadditions of quinolon...
  
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29. Scheme 28: Bifunctional hydrogen bonding/photocatalysed [2 + 2] photocycloaddition reactions. (a) First use of...
  
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30. Scheme 29: Bifunctional hydrogen bonding/photocatalysed deracemisation of allenes.
  
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31. Scheme 30: Bifunctional hydrogen bonding/photocatalysed deracemisation reactions. (a) Deracemisation of sulfox...
  
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32. Scheme 31: Bifunctional hydrogen bonding/photocatalysed intramolecular [2 + 2] photocycloaddition of coumarins....
  
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33. Scheme 32: Bifunctional hydrogen bonding/photocatalysed [2 + 2] photocycloadditions of quinolones. (a) Intramo...
  
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34. Scheme 33: Hydrogen bonding/photocatalysed formal arylation of benzofuranones.
  
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35. Scheme 34: Hydrogen bonding/photoredox-catalysed dehalogenative protonation of α,α-chlorofluoro ketones.
  
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36. Scheme 35: Hydrogen bonding/photoredox-catalysed reductions. (a) Reduction of 1,2-diketones. (b) Reduction of ...
  
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37. Scheme 36: Hydrogen bonding/HAT/photocatalysed deracemisation of cyclic ureas.
  
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38. Scheme 37: Hydrogen bonding/HAT/photoredox-catalysed synthesis of cyclic sulfonamides.
  
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39. Scheme 38: Hydrogen bonding/photoredox-catalysed reaction between imines and indoles.
  
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40. Scheme 39: Chiral cation/photoredox-catalysed radical coupling of two α-amino radicals.
  
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41. Scheme 40: Chiral phosphate/photoredox-catalysed hydroetherfication of alkenols.
  
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42. Scheme 41: Chiral phosphate/photoredox-catalysed synthesis of pyrroloindolines.
  
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43. Scheme 42: Chiral anion/photoredox-catalysed radical cation Diels–Alder reaction.
  
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44. Scheme 43: Lewis acid/photoredox-catalysed cycloadditions of carbonyls. (a) Formal [2 + 2] cycloaddition of en...
  
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45. Scheme 44: Lewis acid/photoredox-catalysed RCA reaction using a scandium Lewis acid between α-amino radicals a...
  
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46. Scheme 45: Lewis acid/photoredox-catalysed RCA reaction using a copper Lewis acid between α-amino radicals and...
  
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47. Scheme 46: Lewis acid/photoredox-catalysed synthesis of 1,2-amino alcohols from aldehydes and nitrones using a...
  
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48. Scheme 47: Lewis acid/photocatalysed [2 + 2] photocycloadditions of enones and alkenes.
  
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49. Scheme 48: Meggers’s chiral-at-metal catalysts.
  
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50. Scheme 49: Lewis acid/photoredox-catalysed α-functionalisation of ketones with alkyl bromides bearing electron...
  
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51. Scheme 50: Bifunctional Lewis acid/photoredox-catalysed radical coupling reaction using α-chloroketones and α-...
  
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52. Scheme 51: Lewis acid/photocatalysed RCA of enones. (a) Using aldehydes as acyl radical precursors. (b) Other ...
  
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53. Scheme 52: Bifunctional Lewis acid/photocatalysis for a photocycloaddition of enones.
  
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54. Scheme 53: Lewis acid/photoredox-catalysed RCA reactions of enones using DHPs as radical precursors.
  
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55. Scheme 54: Lewis acid/photoredox-catalysed functionalisation of β-ketoesters. (a) Hydroxylation reaction catal...
  
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56. Scheme 55: Bifunctional copper-photocatalysed alkylation of imines.
  
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57. Scheme 56: Copper/photocatalysed alkylation of imines. (a) Bifunctional copper catalysis using α-silyl amines....
  
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58. Scheme 57: Bifunctional Lewis acid/photocatalysed intramolecular [2 + 2] photocycloaddition.
  
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59. Scheme 58: Bifunctional Lewis acid/photocatalysed [2 + 2] photocycloadditions (a) Intramolecular cycloaddition...
  
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60. Scheme 59: Bifunctional Lewis acid/photocatalysed rearrangement of 2,4-dieneones.
  
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61. Scheme 60: Lewis acid/photocatalysed [2 + 2] cycloadditions of cinnamate esters and styrenes.
  
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62. Scheme 61: Nickel/photoredox-catalysed arylation of α-amino acids using aryl bromides.
  
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63. Scheme 62: Nickel/photoredox catalysis. (a) Desymmetrisation of cyclic meso-anhydrides using benzyl trifluorob...
  
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64. Scheme 63: Nickel/photoredox catalysis for the acyl-carbamoylation of alkenes with aldehydes using TBADT as a ...
  
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65. Scheme 64: Bifunctional copper/photoredox-catalysed C–N coupling between α-chloro amides and carbazoles or ind...
  
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66. Scheme 65: Bifunctional copper/photoredox-catalysed difunctionalisation of alkenes with alkynes and alkyl or a...
  
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67. Scheme 66: Copper/photoredox-catalysed decarboxylative cyanation of benzyl phthalimide esters.
  
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68. Scheme 67: Copper/photoredox-catalysed cyanation reactions using TMSCN. (a) Propargylic cyanation (b) Ring ope...
  
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69. Scheme 68: Palladium/photoredox-catalysed allylic alkylation reactions. (a) Using alkyl DHPs as radical precur...
  
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70. Scheme 69: Manganese/photoredox-catalysed epoxidation of terminal alkenes.
  
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71. Scheme 70: Chromium/photoredox-catalysed allylation of aldehydes.
  
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72. Scheme 71: Enzyme/photoredox-catalysed dehalogenation of halolactones.
  
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73. Scheme 72: Enzyme/photoredox-catalysed dehalogenative cyclisation.
  
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74. Scheme 73: Enzyme/photoredox-catalysed reduction of cyclic imines.
  
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75. Scheme 74: Enzyme/photocatalysed enantioselective reduction of electron-deficient alkenes as mixtures of (E)/(Z...
  
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76. Scheme 75: Enzyme/photoredox catalysis. (a) Deacetoxylation of cyclic ketones. (b) Reduction of heteroaromatic...
  
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77. Scheme 76: Enzyme/photoredox-catalysed synthesis of indole-3-ones from 2-arylindoles.
  
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78. Scheme 77: Enzyme/HAT/photoredox catalysis for the DKR of primary amines.
  
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79. Scheme 78: Bifunctional enzyme/photoredox-catalysed benzylic C–H hydroxylation of trifluoromethylated arenes.
  
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Beilstein J. Org. Chem. 2020, 16, 2363–2441, doi:10.3762/bjoc.16.197

Full Text

Synthesis and optoelectronic properties of benzoquinone-based donor–acceptor compounds

Daniel R. Sutherland,
Nidhi Sharma,
Georgina M. Rosair,
Ifor D. W. Samuel,
Ai-Lan Lee and
Eli Zysman-Colman

Full Research Paper
Published 04 Dec 2019

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1. Graphical Abstract
2. Scheme 1: Mild and direct C–H monofunctionalization of BQ 1: previous [14] and this work.
  
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3. Figure 1: Benzoquinone derivatives synthesized for this study, with the donor in red and the benzoquinone acc...
  
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4. Scheme 2: Synthesis of 2–4 via mild and direct C–H monofunctionalization of BQ (1).
  
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5. Scheme 3: Synthesis of 5 via double Suzuki coupling.
  
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6. Figure 2: Crystal structures of 3 and 4.
  
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7. Figure 3: HOMO/LUMO and S₁/T₁ energies as well as HOMO/LUMO electron density distribution profiles of 2–5.
  
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8. Figure 4: Cyclic voltammograms and differential pulse voltammograms of 2–5 in degassed DCM (scan rate = 100 m...
  
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9. Figure 5: UV–vis absorption spectra of 2–5 in DCM and photoluminescence spectrum of 3 in degassed DCM and in ...
  
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10. Figure 6: Time-resolved PL plots. a) Prompt decay and b) delayed decay curve of 3 in thin film (λ_exc = 378 nm...
  
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Supp. Info

Beilstein J. Org. Chem. 2019, 15, 2914–2921, doi:10.3762/bjoc.15.285

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Recent advances in materials for organic light emitting diodes

Eli Zysman-Colman

Editorial
Published 27 Jul 2018

Beilstein J. Org. Chem. 2018, 14, 1944–1945, doi:10.3762/bjoc.14.168

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Copper-catalyzed asymmetric sp³ C–H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst

Pierre Querard,
Inna Perepichka,
Eli Zysman-Colman and
Chao-Jun Li

Full Research Paper
Published 06 Dec 2016

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1. Graphical Abstract
2. Scheme 1: Design light-mediated arylation of THIQs.
  
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3. Figure 1: Reaction scope. Reaction conditions: THIQs (0.10 mmol), arylboronic acid (0.30 mmol), TBHP (0.2 mmo...
  
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4. Scheme 2: Evaluation of chiral ligands.
  
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5. Scheme 3: Proposed reaction mechanism.
  
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Supp. Info

Beilstein J. Org. Chem. 2016, 12, 2636–2643, doi:10.3762/bjoc.12.260

Full Text

Recent developments in enantioselective photocatalysis

Synthesis and optoelectronic properties of benzoquinone-based donor–acceptor compounds

Recent advances in materials for organic light emitting diodes

Copper-catalyzed asymmetric sp³ C–H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst

Other Beilstein-Institut Open Science Activities

Keep Informed

Recent developments in enantioselective photocatalysis

Synthesis and optoelectronic properties of benzoquinone-based donor–acceptor compounds

Recent advances in materials for organic light emitting diodes

Copper-catalyzed asymmetric sp3 C–H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst

Other Beilstein-Institut Open Science Activities

Keep Informed

Copper-catalyzed asymmetric sp³ C–H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst